Basic information
- CAS
142128-59-4- Standard SMILES
CC(=O)N1CCN(c2ccc(OC[C@H]3CO[C@](Cn4ccnc4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1- InChIKey
XMAYWYJOQHXEEK-OZXSUGGESA-N- Molecular formula
- C26H28Cl2N4O4
- Average molar mass
- 531.4 g/mol
- Monoisotopic mass
- 530.1487608
Overview
(2R,4S)-ketoconazole is a cis-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine which dioxolane moiety has (2R,4S)-configuration. It is an enantiomer of a (2S,4R)-ketoconazole.
Names & identifiers
- Preferred name
- (2R,4S)-Ketoconazole
- IUPAC
- 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
- English name
- (+)-Ketoconazole
- Molecular formula
- C26H28Cl2N4O4
- Molecular weight
- 531.43
Names & synonyms
(2R,4S)-ketoconazoleCHEBI:483361-acetyl-4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine1-acetyl-4-(4-(((2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazineRefChem:934745(+)-Ketoconazole142128-59-41-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanoneCPD000058460CHEMBL75MFCD00058579Ethanone, 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]-
Show more names
(+)-R 41400(+)-KetoconazolDextroketoconazole((addition))-Ketoconazole(+) Ketoconazole,(+)Ketoconazole
C26H28Cl2N4O4SMR000058460MLS000069784MLS0011469341-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-oneKTZSR-01000075626
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 69.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 735
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
217.3 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID7029879]
213.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
214.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
216.1 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]
Physicochemical properties
- Boiling point
- 753.4 · 753.4±60.0 °C(Predicted)
- Density
- 1.38 · 1.38±0.1 g/cm3(Predicted)
- solubility
- 25.5 mg/mL · ≥25.5 mg/mL in DMSO with gentle warming; insoluble in H2O; insoluble in EtOH
- form
- solid
- pka
- 6.88 · 6.88±0.12(Predicted)
- color
- White to off-white
Chemistry & industry
Pharmacology
ATC CodeD01AC08
Applications
Uses(+)-Ketoconazole can be used in pharmacological activity and biological study as ketoconazole stereoisomers differentially induce CYP4501A1 in human and mouse hepatoma. Enantiomerically pure isomer of racemic Ketoconazole (K186000).
Suppliers19 total
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Aladdin Scientific[email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
大赛璐药物手性技术（上海）有限公司021-50460086-9 15921403865 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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